Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2011(8): 1113-1116
DOI: 10.1055/s-0030-1259933
DOI: 10.1055/s-0030-1259933
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
The Catalytic Addition of Alkyl Boranes to Alkynyl Esters Affording Single-Isomer Trisubstituted Olefins
Further Information
Received
16 February 2011
Publication Date:
30 March 2011 (online)
Publication History
Publication Date:
30 March 2011 (online)
![](https://www.thieme-connect.de/media/synlett/201108/lookinside/thumbnails/10.1055-s-0030-1259933-1.jpg)
Abstract
The generation of a series of trisubstituted olefins bearing alkyl substituents is described using a stereoselective and regioselective addition to alkynyl esters. The method produces trisubstituted olefins as single isomers using a convenient and mild transformation in which alkyl boranes are cross-coupled with alkynyl esters and amides using palladium catalysis.
Key words
olefination - stereoselectivity - regioselectivity - cross-coupling - asymmetric synthesis
-
1a
Valentine DH.Hillhouse JH. Synthesis 2003, 317 -
1b
Rein T.Pedersen TM. Synthesis 2002, 579 -
1c
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863 -
1d
Iorga B.Eymery F.Mouriès V.Savignac P. Tetrahedron 1998, 54: 14637 -
1e
Wadsworth WS. Org. React. 1977, 25: 73 -
1f
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4490 -
1g
Grubbs RH. Tetrahedron 2004, 60: 7117 -
2a
Tan Z.Negishi E. Angew. Chem. Int. Ed. 2006, 45: 762 -
2b
Tan Z.Negishi E.-I. Angew. Chem. 2006, 118: 776 -
2c
Marek I. Chem. Rev. 2000, 100: 2887 -
2d
Hata T.Kitagawa H.Masai H.Kurahashi T.Shimizu M.Hiyama T. Angew. Chem. 2001, 113: 812 -
2e
Hata T.Kitagawa H.Masai H.Kurahashi T.Shimizu M.Hiyama T. Angew. Chem. Int. Ed. 2001, 40: 790 -
2f
Kurahashi T.Hata T.Masai H.Kitagawa H.Shimizu M.Hiyama T. Tetrahedron 2002, 58: 6381 -
2g
Itami K.Mineno M.Muraoka N.Yoshida J. J. Am. Chem. Soc. 2004, 126: 11778 -
2h
Rossi R.Bellina F.Carpita A.Mazzarella F. Tetrahedron 1996, 52: 4095 -
2i
Normant JF.Alexakis A. Synthesis 1981, 841 -
2j
Corey EJ.Katzenellenbogen JA. J. Am. Chem. Soc. 1969, 91: 1851 -
2k
Negishi E.-i.Zhang Y.Cederbaum FE.Webb MB. J. Org. Chem. 1986, 51: 4080 -
2l
Itami K.Yoshida J.-i. Bull. Chem. Soc. Jpn. 2006, 79: 811 -
2m
Itami K.Yoshida J.-i. Chem. Eur. J. 2006, 12: 3966 -
3a
Chen C.Kehr G.Fröhlich R.Erker G. J. Am. Chem. Soc. 2010, 132: 13594 -
3b
Zhou C.-Y.Zhu S.-F.Wang L.-X.Zhou Q.-L. J. Am. Chem. Soc. 2010, 132: 10955 -
3c
Tsuji H.Ueda Y.Ilies L.Nakamura E. J. Am. Chem. Soc. 2010, 132: 11854 -
3d
Nakao Y.Yada A.Hiyama T. J. Am. Chem. Soc. 2010, 132: 10024 -
3e
Yang C.-M.Jeganmohan M.Parthasarathy K.Cheng C.-H. Org Lett. 2010, 132: 3610 -
3f
Hayashi T.Inoue K.Taniguchi N.Ogasawara M. J. Am. Chem. Soc. 2001, 123: 9918 -
3g
Hall DG.Chapdelaine D.Préville P.Deslongchamps P. Synlett 1994, 660 -
3h
Houpis IN.Lee J. Tetrahedron 2000, 56: 817 -
3i
Qian M.Huang Z.Negishi E. Org. Lett. 2004, 6: 1531 -
3j
Pommier A.Stepanenko V.Jarowicki K.Kocienski PJ. J. Org. Chem. 2003, 68: 4008 -
3k
Konno T.Daitoh T.Noiri A.Chae J.Ishihara T.Yamanaka H. Org. Lett. 2004, 6: 933 -
3l
Nishihara Y.Miyasaka M.Okamoto M.Takahashi H.Inoue E.Tanemura K.Takagi K. J. Am. Chem. Soc. 2007, 129: 12634 -
4a
Corbet J.-P.Mignani G. Chem. Rev. 2006, 106: 2651 -
4b
Kinney WA.Teleha CA.Thompson AS.Newport M.Hansen R.Ballentine S.Ghosh S.Mahan A.Grasa G.Zanotti-Gerosa A.Dingenen J.Schubert C.Zhou Y.Leo GC.McComsey DF.Santulli RJ.Maryanoff BE. J. Org. Chem. 2008, 73: 2302 -
4c
Molander GA.Yokoyama Y. J. Org. Chem. 2006, 71: 2493 -
4d
Liron F.Fosse C.Pernolet A.Roulland E. J. Org. Chem. 2007, 72: 2220 -
4e
Tan Z.Negishi E.-I. Angew. Chem. Int. Ed. 2006, 45: 762 - 5
Bush AG.Jiang JL.Payne PR.Ogilvie WW. Tetrahedron 2009, 65: 8502 -
6a
Lin P.-S.Jeganmohan M.Cheng C.-H. Chem. Eur. J. 2008, 14: 11296 -
6b
Kuº M.Artok A.Ziyanak F.Artok L. Synlett 2008, 2587 -
6c
Yamamoto Y.Kirai N. Org. Lett. 2008, 10: 5513 -
6d
Trost BM.Matsubara S.Caringi JJ. J. Am. Chem. Soc. 1989, 111: 8745 -
6e
Trost BM.McIntosh MC. J. Am. Chem. Soc. 1995, 117: 7255 -
6f
Trost BM.Frontier AJ. J. Am. Chem. Soc. 2000, 122: 11727 -
6g
Lindhardt AT.Mantel MLH.Skrydstrup T. Angew. Chem. Int. Ed. 2008, 47: 2668 -
6h
Yamamoto Y.Kirai N.Harada Y. Chem. Commun. 2008, 2010 -
7a
Oh CH.Jung HH.Kim KS.Kim N. Angew. Chem. Int. Ed. 2003, 42: 805 -
7b
Oh CH.Ryu JH. Bull. Korean Chem. Soc. 2003, 24: 1563 -
7c
Gupta AK.Kim KS.Oh CH. Synlett 2005, 457 -
8a
Simard-Mercier J.Jiang JL.Ho ML.Flynn AB.Ogilvie WW. J. Org. Chem. 2008, 73: 5899 -
8b
Rajagopal T.Flynn AB.Ogilvie WW. Tetrahedron 2010, 66: 8739